Triethylamine → 1,1-Dimethylethyl [(2R)-2-hydroxy-2-phenylethyl]carbamate

HRID 2054544Notes

Reaction equation

HRID 2054544 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH3:11][C:12]([O:15][C:16](=O)[O:17]C(C)(C)C)([CH3:14])[CH3:13].C(N(CC)CC)C>CO>[OH:4][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][NH:1][C:16](=[O:17])[O:15][C:12]([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6951165(R)-(-)-2-Amino-1-phenylethanolHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 114817921,1-Dimethylethyl [(2R)-2-hydroxy-2-phenylethyl]carbamateYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-α-(Aminomethyl)benzenemethanol (1.70 g) and bis(1,1-dimethylethyl)carbonate (2.98 g) were dissolved in methanol (20 ml) and triethylamine (4.3 ml) added. The mixture was stirred at room temperature for 4 days and then concentrated to leave the sub-title compound as an oil (2.60 g).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d00a954de056464b938d25d7f2aca14b
Source dataset
uspto-grants-2008_02
Patent number
US07329686B2

Reaction notes

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